Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From ketone or ketene reactant
Patent
1995-08-28
1998-01-27
Hampton-Hightower, P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From ketone or ketene reactant
528228, 528246, 528263, 528266, 525259, 5253282, 5253284, 525382, 525421, 525449, 525455, 525471, 525530, 525531, C08F 830, C08G 1200
Patent
active
057123632
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
The present invention relates generally to oligomeric sterically hindered polyamines and their use as replacements for traditional amine crosslinkers, particularly in the coatings field.
Compositions based upon polyamine crosslinkers and compounds containing amine-reactive functionality are well-known in the literature. As examples of such amine-reactive functionality in combination with polyamine crosslinkers may be mentioned: groups derived from maleic acid and anhydride, fumaric acid, itaconic acid and anhydride, and crotonic acid and anhydride (see, e.g., U.S. Pat. Nos. 2,759,913, 4,251,597, 4,303,563, 4,730,033, 4,871,822, 4,981,944, 4,990,577, 5,011,994, 5,112,904, WO-A-92/07010, EP-A-568134; U.S. Pat. Nos. 3,668,183, 4,772,680, 4,929,661, 5,011,994, WO-A-92/07010, EP-A-568134 3,793,417, 3,945,964, 4,126,640, 4,193,905, 4,315,044, 4,318,832, 4,352,898, 4,362,856, 4,489,179, 4,503,174, 4,598,108, 4,608,406, 4,737,530, 5,011,994, WO-A-92/07010, GB-A-1229840, EP-A-568134 3,793,417, 5,011,994, 5,072,020); WO-A-92/07010, EP-A-568134 JP-A-01146966, JP-A-01146968, JP-A-02053880, WO-A-92/07010, EP-A-568134; and 4,279,793, 4,522,973, 4,588,783, 4,755,623, 4,904,740, 4,937,293, 5,011,994, 5,089,565), including oxalate esters (see, e.g., U.S. Pat. No. 4,414,250, DE-A-4036984, WO-A-92/07010, EP-A-568134.
In general, conventional polyamine crosslinkers with primary amino groups are quite reactive with the above-functionalities under ambient or low stoving temperature conditions (<100.degree. C.). This can result in a too short potlife and consequent application problems.
Acyclic aliphatic secondary amines have also been utilized; however, they exhibit insufficient reactivity towards many of the above-mentioned functionalities, which can lead to improper crosslinking performance.
There thus exists a reactivity gap between the conventional primary and secondary amino groups-containing crosslinkers which as been somewhat filled by the blocking of the primary amino groups with, for example, ketones and aldehydes resulting in, respectively, ketimines and aldimines. The reaction sequence is as follows: ##STR1##
The resulting imine group is stable under anhydrous conditions, but unstable even in the presence of atmospheric humidity. This property has been utilized quite successfully in low and ambient temperature cure applications. The use of ketimines/aldimines, ever, has certain disadvantages.
For example, the deblocking of the primary amino group results in the liberation of a volatile ketone or aldehyde. This liberated component not only adds to the overall VOC of the system, but can also lave toxicological consequences and, under certain circumstances, detrimental consequences to the appearance characteristics of the resulting crosslinked products (e.g., low depth of reflected image in clearcoat applications).
Further in this respect, in light of tougher environmental laws industry has been seeking waterborne alternatives to their longstanding organic solvent based products. Ketimines/aldimines as indicated above, are water sensitive--their hydrolysis is generally so fast that there is no possibility left for controlling reactivity. They are also more hydrophobic than their amine counterparts. It has, therefore, been difficult to formulate waterborne systems utilizing these crosslinkers.
It is, therefore, an object of the present invention to provide a suitable alternative which overcomes these disadvantages of the traditional polyamine and blocked polyamine crosslinkers.
SUMMARY OF THE INVENTION
In accordance with the present invention, the traditional polyamine and blocked polyamine crosslinkers are replaced with certain oligomeric sterically hindered polyamines which comprise, in their overall concept, a backbone having pendant therefrom at least two amino groups, characterized in that (Mn) in the range of 200-10000, more preferably 250-3000, and especially 250-2000.
Suitable oligomeric sterically hindered polyamines can be produced, for example, by one of the following methods
REFERENCES:
patent: 2759913 (1956-08-01), Hulse
patent: 3291775 (1966-12-01), Holm
patent: 3419534 (1968-12-01), Goodman et al.
patent: 3535342 (1970-10-01), Emmons
patent: 3547886 (1970-12-01), Gardner et al.
patent: 3621000 (1971-11-01), Schmelzer et al.
patent: 3657192 (1972-04-01), Schulz et al.
patent: 3668183 (1972-06-01), Hoy et al.
patent: 3793417 (1974-02-01), Erikson et al.
patent: 3945964 (1976-03-01), Hastings et al.
patent: 4126640 (1978-11-01), Floyd
patent: 4193905 (1980-03-01), Audykowski et al.
patent: 4251597 (1981-02-01), Emmons et al.
patent: 4279793 (1981-07-01), Wellner et al.
patent: 4303563 (1981-12-01), Emmons et al.
patent: 4315044 (1982-02-01), Elmore et al.
patent: 4318832 (1982-03-01), Zabrocki et al.
patent: 4352898 (1982-10-01), Albers
patent: 4362856 (1982-12-01), Kluger
patent: 4414250 (1983-11-01), Costanza et al.
patent: 4489179 (1984-12-01), Tortorello
patent: 4503174 (1985-03-01), Vasta
patent: 4522973 (1985-06-01), Ley et al.
patent: 4588783 (1986-05-01), Chang
patent: 4598108 (1986-07-01), Hoefs
patent: 4608406 (1986-08-01), Williams, Jr. et al.
patent: 4730033 (1988-03-01), Horley et al.
patent: 4737530 (1988-04-01), Hoefs et al.
patent: 4755623 (1988-07-01), Dileone
patent: 4772680 (1988-09-01), Noomen et al.
patent: 4835289 (1989-05-01), Brindopke
patent: 4871822 (1989-10-01), Brindopke et al.
patent: 4892954 (1990-01-01), Brindopke et al.
patent: 4904740 (1990-02-01), Blum et al.
patent: 4929661 (1990-05-01), Noomen et al.
patent: 4937293 (1990-06-01), Blum et al.
patent: 4981944 (1991-01-01), Bartels et al.
patent: 4990577 (1991-02-01), Noomen et al.
patent: 5011994 (1991-04-01), Bartels et al.
patent: 5071481 (1991-12-01), Maters et al.
patent: 5072020 (1991-12-01), Speranza et al.
patent: 5089565 (1992-02-01), Blum et al.
patent: 5112904 (1992-05-01), Feith
patent: 5140057 (1992-08-01), Saeki et al.
Kirk-Othmer, Encyclopedia of Chemical Technology, vol. 2, pp. 355-376 (1978).
*PCT International Search Report in PCT/EP94/00015 dated May 4, 1994.
Hobel Klaus
Mezger Thomas
Noomen Arie
van den Berg Keimpe Jan
Akzo Nobel nv
Hampton-Hightower P.
Miraglia Loretta A.
Morris Louis A.
LandOfFree
Oligomeric sterically hindered polyamine crosslinkers and coatin does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Oligomeric sterically hindered polyamine crosslinkers and coatin, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oligomeric sterically hindered polyamine crosslinkers and coatin will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-343248